Pyridine → 5-[5-(tert-Butoxycarbonylamino-methyl)-2-chloro-benzoylamino]-2-[2-(methoxy)ethoxy]-benzoic acid

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Reaction Steps

1-Chloro-N,N,2-trimethylpropenylamine (166 μL; 1.25 mmol) was added to a mixture of 5-(tert-butoxycarbonylamino)methyl-2-chloro benzoic acid (263 mg; 0.92 mmol) in MeCN (10 mL) and stirred at rt for 15 min. Pyridine (198 μL; 2.51 mmol) and 5-amino-2-(2-methoxyethoxy)-benzoic acid ethyl ester (200 mg; 0.84 mmol) was added and it was stirred at rt overnight. The mixture was filtered through a pad of Alox B, washed with DMF/MeOH 9/1 and concentrated i. vac. The residue was mixed with 15 mL MeOH and 15 mL 2 M aq NaOH and stirred for 3 days at rt. After concentration, the residue was diluted with 10 mL 4M aq. HCl, extracted with EtOAc, dried with Na2SO4 and concentrated i. vac. The crude was mixed with 50 mL Dioxan; 5 mL H2O and di-tert-butyldicarbonate (200 mg), stirred at rt for 2 h and concentrated. Yield: 380 mg (95%); MS: [M+H]+=479 (Cl isotope pattern); HPLC: Rt=2.01 min (Method CC-4)

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